Adamantane, due to its unique structure and stability, has the potential to be used in a number of applications including advanced materials, ligands for transition metal catalysis, and scaffolds for drug molecules. The current scope of transformations that can be performed on adamantane are largely limited to oxidation and bromination reactions. Within these known transformations, the bulk of them are directed at the bridge-head position of the cage, as the bridge-head bromination of adamantane is a straight-forward reaction to perform. Our research focuses on the synthesis and characterisation of previously inaccessible adamantane derivatives including higher polymantanes (diamantane, triamantane, etc.) via C-H bond activation in 2-adamantyl transition metal complexes. By expanding the scope of transformations that can be performed on adamantane, especially at the much more inaccessible bridge position of the cage, the usefulness of diamondoid chemistry could be vastly increased. The synthesis and reactivities of a number of new organometallic adamantyl complexes, as well as their potential for novel functionalizations of adamantane, will be discussed.

Organometallic chemistry of adamantane: Toward novel functionalization of diamondoid hydrocarbons

251st National Meeting (2016)

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